Rob Kardashian Shared The Most Awkward Sex Story On KUWTK

It’s essentially a law of nature that whenever Rob Kardashian graces Keeping Up With The Kardashians with his presence, he will say something to illicit the proverbial side-eye from viewers across America. Remember when he was obsessed with Dream being an Armenian baby and only an Armenian baby? Well, Red Flag Rob returned in the latest season 13, episode "Loyalties And Royalties," to make everyone uncomfortable with a story that put "Kim Kardashian look-alike" and sex in the same sentence.

The cringeworthy antics begin before KUWTK could even get to its first commercial break. After checking in on Kim, Kourtney Kardashian, and Caitlyn Jenner via iPhone, we arrive at Khloe Kardashian’s home while Rob is visiting his period-addled sister. Koko asks if she has a fever and Rob examines her forehead with the back of his hand. It’s actually a pretty sweet show of sibling love. Then it gets weird. Rob slides his hand off of Khloe’s forehead and gently caresses the side of her cheek. Khloe’s only response is laughing, "You’re fucking weird," and bringing up another instance where it seemed Rob could be genuinely attracted to one of his sisters.

"Do you remember when you...fucked the girl that won the Kim Kardashian look-alike contest?" she asks. Rob doesn't deny this ever happened, meaning the famous brother purposefully slept with a woman who looks so much like his sister, she’s won at least one award for it. This gets all the more awkward when you remember Rob’s September 2016 interview with sometimes-fiancée Blac Chyna, where the subject of childhood crushes came up. During the chat, Chyna claims Rob had quite a thing for Kim Kardashian as a young boy. Kim’s little brother agrees he had a crush on her, saying with a small nod, "That is also pretty accurate." Then Chyna confirms this isn’t a bizarre joke, declaring, "These are facts."

As a way to make Khloe forget about his apparent long-held attraction to one of his older sisters, Rob brings up a different head scratcher of a sex story. "Oh, I thought you were talking about the girl that pulled up to your house and she was, like butt naked, and then I went upstairs, had sex with her, and she perioded all over the bed," he word vomits at Koko. The reason this story is terrible isn’t because a woman had sex on her period — you go, girl! Whoever you are! — it’s terrible because of how immature Rob sounds. First of all, "perioded," Rob? You’re a grown man with a daughter and that’s how you talk about a totally normal and necessary human function? Secondly, it sure sounds like Rob is dragging a girl for having sex with him. Because that’s not misogynistic or anything.

Despite Rob’s attempt to sound like a 12-year-old boy in health class as a means of distraction, Khloe still brings the conversation back to the time he slept with that Kim doppelgänger. "Why didn’t you ever sleep with someone who won a Khloe Kardashian look-alike contest?" she asks, looking up at Rob from her bed. Yes, we would all like to erase that sentence from our minds, but, alas, that's impossible. At least we can all praise the Lord (Disick) that Kourtney Kardashian has yet to be connected to her baby brother's sexual exploits in any way, shape, or form.